Synthesis of Chiral Aziridines

Technology #ua16-006

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Researchers
Isaac Chogii
Graduate Assistant, Chemistry & Biochemistry
Jon Njardarson
Professor, Chemistry & Biochemistry
Managed By
Paul Eynott
Sr. Licensing Manager (520) 621-2878

Title: One Pot Synthesis of Aziridine

Invention: The invention describes a way to produce chiral aziridine compounds in a one-pot reaction with no metal catalysts. This can offer a significantly reduced cost of production to manufacturers that utilize aziridine.

Background: Existing aziridine synthetic routes can seldom be done in a one step pathway. Furthermore, many syntheses require the uses of metal catalysts to achieve workable yield and still produce potential secondary products that are irrelevant to the use cases at hand.

Applications:

The synthesis can be applied to creating biofoul resistant coatings for medical devices

Hardening agent for a variety of compounds

Advantages:

One pot synthetic reaction makes creating the compound relatively simple and cuts out costs that would have been associated with extra steps.

No metal components will also reduce costs from standard aziridine synthesis

Chiral output allows selective compounds to be developed and reduces waste and secondary products 

Related Publications:

Ilardi, E. a., & Njardarson, J. T. (2013). Ring expansions of vinyloxiranes, -thiiranes, and -aziridines: Synthetic approaches, challenges, and catalytic success stories. Journal of Organic Chemistry, 78(19), 9533–9540. http://doi.org/10.1021/jo401776s

Rogers, E., Araki, H., Batory, L. a., McInnis, C. E., & Njardarson, J. T. (2007). Highly selective copper-catalyzed ring expansion of vinyl thiiranes: Application to synthesis of biotin and the heterocyclic core of plavix. Journal of the American Chemical Society, 129(10), 2768–2769. http://doi.org/10.1021/ja069059h

J. T. Njardarson, Catalytic ring expansion adventures. Synlett 24, 787–803 (2013). CrossRefWeb of ScienceGoogle Scholar

Licensing Manager: 

Name: Paul Eynott

Email: paule@tla.arizona.edu

Phone: 520.471.2687

Technology ID: UA16-006

Inventors: Jon Njardarson and Isaac Chogii